CN105801333B - A kind of preparation method of coronene - Google Patents
A kind of preparation method of coronene Download PDFInfo
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- CN105801333B CN105801333B CN201610285253.7A CN201610285253A CN105801333B CN 105801333 B CN105801333 B CN 105801333B CN 201610285253 A CN201610285253 A CN 201610285253A CN 105801333 B CN105801333 B CN 105801333B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Abstract
The invention discloses a kind of preparation method of coronene.Preparation in accordance with the present invention, this method include：Coupling reaction：Compound carries out coupling reaction with compound shown in the Formula II of 4.2~5.6 equivalents shown in the Formulas I of 1 equivalent, is converted into compound shown in formula III；Ring closure reaction：Compound shown in formula III carries out ring closure reaction in presence of an acid, is converted into the coronene shown in formula IV；
Description
Technical field
The invention belongs to organic fluorescence materials to synthesize field, more particularly to a kind of preparation method of coronene.
Background technology
Coronene is a kind of organic fluorescence materials.Maximum absorption wave a length of 255nm, the maximum emission wavelength 520nm of coronene,
And there is high-quantum efficiency, therefore, coronene can be used in ultraviolet-charge coupling device, can be used in radar.
At present, the preparation method on coronene mainly includes following three kinds：
The first is preparations of the Joost T.M.van Dijk disclosed in J.Org.Chem.1996,61,1136-1139
Method, the chemical equation of this method are as follows：
In the method, need to be with being cooled to -60 DEG C, not easy to operate, reactions steps are more and cumbersome, therefore are not suitable for big
Large-scale production；
Second is the preparation disclosed in J.Org.Chem.2005,70,10113-10116 such as Shen, Hung-Chin
Method, the chemical equation of this method are as follows：
In the method, the catalyst TpRuPPh that the reaction time needs 30 hours and used3(CH3CN)PF6Price is held high
It is expensive, be not suitable for large-scale production；
The third is Zhu Yulan etc. in New Chemical Materials 2013,41 (3), the preparation method disclosed in 34-35, this method
Chemical equation it is as follows：
In the method, need to reach 200 by two step Diels-Alder reactions and two step decarboxylic reactions, reaction temperature
DEG C, condition is harsh, and reactions steps are more, and overall yield of reaction is only 46%.
The content of the invention
The invention provides a kind of preparation method of coronene, it is severe to solve expensive starting materials present in prior art, condition
Carve, cumbersome and low yield technical problem.
According to an aspect of the present invention, there is provided a kind of preparation method of coronene, this method include：
Coupling reaction：Shown in the Formulas I of 1 equivalent chemical combination shown in the Formula II of compound and 4.2~5.6 equivalents catalyst,
Under the conditions of alkali is existing, coupling reaction is carried out in a solvent, is converted into compound shown in formula III；
Ring closure reaction：Compound shown in formula III carries out ring closure reaction in presence of an acid, is converted into the coronene shown in formula IV；
Alternatively, preparation in accordance with the present invention, in the coupling reaction, the catalyst is selected from four triphenylphosphines
Palladium, Pd/C, two (triphenylphosphine) palladium chlorides；The alkali is selected from potassium carbonate, sodium carbonate, sodium hydroxide, three hypophosphite monohydrate potassium, nothing
Water potassium phosphate.
Alternatively, preparation in accordance with the present invention, in the coupling reaction, the dosage of compound shown in Formula II is
4.4~5.0 equivalents.
Alternatively, preparation in accordance with the present invention, the solvent of the coupling reaction are mixture, the first of toluene and ethanol
The mixture of benzene and methanol, the mixture of toluene and second alcohol and water, mixture, tetrahydrofuran, the tetrahydrofuran of DMF, DMF and water
The mixture of mixture, dioxane, dioxane and water with water, glycol dimethyl ether, glycol dimethyl ether and water it is mixed
Compound.
Alternatively, preparation in accordance with the present invention, in the coupling reaction, reaction temperature is 60~90 DEG C, reaction
Time is 4~10 hours.
Alternatively, preparation in accordance with the present invention, in the cyclization step, the acid is Loprazolam or fluoroform sulphur
Acid.
Alternatively, preparation in accordance with the present invention, the Loprazolam or trifluoromethanesulfonic acid are 5~18 equivalents.
Alternatively, preparation in accordance with the present invention, the cyclization step are reacted in dichloromethane solvent.
Alternatively, preparation in accordance with the present invention, when the acid is Loprazolam, solvent is dichloromethane；Wherein,
The Loprazolam is added dropwise to reaction system at -10~0 DEG C；
After the Loprazolam is added dropwise, reaction system reacts 90min at 20~30 DEG C, obtains swooning shown in formula IV
Benzene.
The present invention has the beneficial effect that：
Preparation in accordance with the present invention, technique is simple, reaction condition is gentle, easily operation；Required raw material is easy to get, cost
It is cheap, therefore it is adapted to large-scale production.
Embodiment
Specific embodiment is only the description of the invention, below will knot without forming the limitation to present invention
Close specific embodiment the present invention is further described and described.
According to the preparation method of coronene of the present invention, this method includes：
Substitution reaction：Compound is being catalyzed with compound shown in the Formula II of 4.2~5.6 equivalents shown in the Formulas I of 1 equivalent
Under the conditions of agent, auxiliary agent are existing, coupling reaction is carried out in a solvent, is converted into compound shown in formula III；
Ring closure reaction：Compound shown in formula III carries out ring closure reaction in presence of an acid, is converted into the coronene shown in formula IV；
Coronene Chinese nickname is cool, molecular formula C24H12, also known as coronene, it is to be condensed around one kind by six phenyl ring
Form, the symmetrical polycyclic aromatic hydrocarbons (PAH) of structure height；Coronene shows bluish violet fluorescence in organic solvent.
In the preparation method of coronene of the present invention, preparation method is simple using two reactions of coupling and cyclization, technique；From
Compound shown in compound shown in Formulas I and Formula II is raw material, and selected raw material is easy to get, cost is cheap；Compound shown in Formulas I and Formula II
When the dosage of shown compound uses above-mentioned dosage, can react fully generation, and be down to amount of by-products caused by reaction
It is minimum, increase the purity of product, improve yield.
According to one embodiment of the present invention, in coupling reaction, catalyst is selected from tetra-triphenylphosphine palladium, Pd/C, and two
(triphenylphosphine) palladium chloride；Alkali is selected from potassium carbonate, sodium carbonate, sodium hydroxide, three hypophosphite monohydrate potassium, anhydrous phosphoric acid potassium.
According to one embodiment of the present invention, the solvent of coupling reaction is mixture, toluene and the first of toluene and ethanol
The mixture of alcohol, the mixture of toluene and second alcohol and water, the mixture of DMF, DMF and water, tetrahydrofuran, tetrahydrofuran and water
Mixture, dioxane, the mixture of dioxane and water, glycol dimethyl ether, the mixture of glycol dimethyl ether and water.
According to the preparation method of coronene of the present invention, compound shown in Formulas I has four reaction sites, therefore the Formulas I institute of 1 equivalent
Show compound, using during compound, can react fully generation, obtain chemical combination described in formula III shown in 4.2 equivalent above formula II
Thing.
The detailed process of coupling reaction is：Under nitrogen protection, by compound shown in the Formulas I of 1 equivalent, 4.2~5.6 equivalents
Compound shown in Formula II, catalyst, alkali and solvent are added in reactor and stirred, and are to slowly warm up to 60~90 DEG C of reactions 4
~10 hours, then cool, add water and organic solvent not soluble in water carries out liquid separation, after organic layer washing, anhydrous sodium sulfate
Dry, filter off drier, silicagel column Removal of catalyst, eluent is concentrated under reduced pressure dry, then cool, add dichloromethane, obtain
Dichloromethane solution containing compound shown in formula III；
According to one embodiment of the present invention, in cyclization step, acid is Loprazolam or trifluoromethanesulfonic acid.
According to the preparation method of coronene of the present invention, Loprazolam used and trifluoromethanesulfonic acid are strong acid, can be effective
Promote the compound shown in formula III to carry out ring closure reaction, obtain the coronene shown in formula IV.
According to one embodiment of the present invention, Loprazolam or trifluoromethanesulfonic acid are 5~18 equivalents.
According to the preparation method of coronene of the present invention, when the dosage of Loprazolam or trifluoromethanesulfonic acid uses above-mentioned dosage,
It can minimize amount of by-products caused by reaction, increase the purity of product, improve product yield.
According to one embodiment of the present invention, cyclization step is reacted in dichloromethane solvent.
According to the preparation method of coronene of the present invention, in substitution reaction, because compound shown in the formula III of generation is in dichloro
Solubility in methane is good, so as to make compound shown in formula III fully be reacted, improves product yield.
According to one embodiment of the present invention, when acid is Loprazolam, solvent is dichloromethane；Wherein,
Loprazolam is added dropwise to reaction system at -10~0 DEG C；
After Loprazolam is added dropwise, reaction system reacts 90~150min at 20~30 DEG C, obtains swooning shown in formula IV
Benzene.
According to the preparation method of coronene of the present invention, Loprazolam is a kind of strong acid, Loprazolam is directly largely added anti-
Ying Zhong, substantial amounts of heat can be released, aggravates reaction, so Loprazolam needs to be added dropwise at low temperature when adding reaction system；Instead
Answer temperature and reaction time to minimize amount of by-products caused by reaction when selecting above-mentioned number range, increase product
Purity, improve product yield.Meanwhile reaction temperature is controlled in -10~0 DEG C and 20~30 DEG C, reaction is abundant, and reaction condition
Gently, it is simple to operate.
The detailed process of cyclization step is：The dichloromethane solution of compound shown in formula III is cooled, by 6~20 equivalents
Slow acid be added dropwise in dichloromethane solution, reaction system is maintained at -10~0 DEG C and is added dropwise to acid；Reaction system is delayed
Slow heating, reaction system react 90min at 20~30 DEG C, obtain the reaction solution of the compound (coronene) shown in IV；By formula IV institute
Show the reacting liquid filtering of compound (coronene), obtain crude product, crude product is washed, methanol washing, obtain coronene.
It is more according to the optional factor that the preparation method of coronene of the present invention provides, can group according to the claim of the present invention
Close out different embodiments, embodiment is only used for that the present invention is described further, does not limit the invention.Below
The present invention will be further detailed in conjunction with the embodiments.
Embodiment 1
Synthetic route is as follows：
According to the preparation method of coronene of the present invention, enter coupling reaction first, under nitrogen protection, by 5.2g (0.01mol,
1eq) compound shown in Formulas I (being prepared according to Eur.J.Org.Chem.2008,994-1004), 8.71g (0.044mol, 4.4eq)
Compound shown in Formula II (is prepared) according to WO2014/37750,0.46g (0.0004mol, 0.04eq) tetra-triphenylphosphine palladium,
12.1g (0.088mol, 8.8eq) potassium carbonate, 80 milliliters of toluene, 60 milliliters of ethanol, add in reactor and stir, slowly
It is warming up to 60~70 DEG C to react 8 hours, is then down to 20 DEG C, adds 100 milliliters of water, 100 milliliters of toluene, stirring, liquid separation, toluene
Layer washing 2 times, is filtered to remove drier after anhydrous sodium sulfate drying, then cross silicagel column, and eluent is concentrated under reduced pressure into dry, addition
80 milliliters of dichloromethane, obtain the dichloromethane solution containing compound shown in formula III.Then cyclization step is carried out, by formula III
The dichloromethane solution cooling of shown compound, 5.8g (0.06mol, 6eq) Loprazolam is slowly added dropwise molten to dichloromethane
In liquid, reaction system is maintained at -7~-10 DEG C and is added dropwise to Loprazolam；Reaction system is to slowly warm up to 20 DEG C of reactions
90min, obtain the reaction solution containing compound (coronene) shown in formula IV；The reaction solution mistake of compound shown in formula IV (coronene) will be contained
Filter, obtains crude product, crude product is washed, methanol is washed, and obtains 2.09g products, product yield 69.67%.
Obtained product fusing point test is subjected to, the fusing point measured is 425.2~427.8 DEG C.
Obtained product is carried out1HNMR is detected,1HNMR spectrum analysis data are as follows：1HNMR (500MHz, CDCl3)：
8.40 (s, 12H).
Obtained product Lc-Ms detections are subjected to, obtained m/e values are 300.
Embodiment 2
The dosage of compound shown in Formula II is simply changed to 4.2 equivalents by 4.4 equivalents, obtained by synthetic method with embodiment 1
1.99g products, product yield 66.33%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 3
The dosage of compound shown in Formula II is simply changed to 4.7 equivalents by 4.4 equivalents, obtained by synthetic method with embodiment 1
2.12g products, product yield 70.67%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 4
The dosage of compound shown in Formula II is simply changed to 5.0 equivalents by 4.4 equivalents, obtained by synthetic method with embodiment 1
2.13g products, product yield 71%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 5
The dosage of compound shown in Formula II is simply changed to 5.6 equivalents by 4.4 equivalents, obtained by synthetic method with embodiment 1
2.11g products, product yield 70.33%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 6
Tetra-triphenylphosphine palladium therein is simply changed etc. into 5% Pd/C of amount of substance, obtained with embodiment 1 by synthetic method
To 2.09g products, product yield 69.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 7
Synthetic method simply changes tetra-triphenylphosphine palladium therein etc. into two (triphenylphosphines) of amount of substance with embodiment 1
Palladium chloride, obtain 2.13g products, product yield 71%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 8
Synthetic method is with embodiment 1, simply by the solvent of coupling reaction by 80 milliliters of toluene, the mixture of 60 milliliters of ethanol
80 milliliters of toluene are changed to, the mixture of 40 ml methanols, obtain 1.88g products, product yield 62.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 9
Synthetic method is with embodiment 1, simply by the solvent of coupling reaction by 80 milliliters of toluene, the mixture of 60 milliliters of ethanol
80 milliliters of toluene are changed to, 60 milliliters of ethanol, the mixture of 30 milliliters of water, obtain 1.76g products, product yield 58.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 10
Synthetic method is with embodiment 1, simply by the solvent of coupling reaction by 80 milliliters of toluene, the mixture of 60 milliliters of ethanol
120 milliliters of DMF are changed to, obtain 2.12g products, product yield 70.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 11
Synthetic method is with embodiment 1, simply by the solvent of coupling reaction by 80 milliliters of toluene, the mixture of 60 milliliters of ethanol
100 milliliters of DMF are changed to, 20 milliliters of water, obtain 2.1g products, product yield 70%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 12
Potassium carbonate is simply changed etc. into the potassium phosphate of amount of substance, obtains 2.21g products, produce with embodiment 10 by synthetic method
Product yield is 73.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 13
Potassium carbonate is simply changed into three hypophosphite monohydrate potassium of equivalent, obtains 2.38g productions by synthetic method with embodiment 10
Product, product yield 79.33%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 14
Coupling reaction therein is simply changed into 5 hours, obtains 2.22g products with embodiment 13 by synthetic method for 8 hours,
Product yield is 74%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 15
Coupling reaction therein is simply changed into 10 hours, obtains 2.40g products with embodiment 13 by synthetic method for 8 hours,
Product yield is 80%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 16
Coupling reaction temperature therein is simply changed into 80~90 DEG C from 60~70 DEG C, obtained by synthetic method with embodiment 13
To 2.36g products, product yield 78.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 17
Loprazolam therein is simply changed into the trifluoromethanesulfonic acid of amount of substance, obtained by synthetic method with embodiment 1
2.08g products, product yield 69.33%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 18
Synthetic method simply changes the amount of Loprazolam into 10 equivalents by 6 equivalents, obtains 2.12g products with embodiment 1,
Product yield is 70.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 19
Synthetic method simply changes the amount of Loprazolam into 13 equivalents by 6 equivalents, obtains 2.16g products with embodiment 1,
Product yield is 72%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
Embodiment 20
Synthetic method simply changes the amount of Loprazolam into 17 equivalents by 6 equivalents, obtains 2.15g products with embodiment 1,
Product yield is 71.66%.
Obtained product fusing point test is subjected to, the fusing point measured is 425~427 DEG C.
As can be seen here, preparation in accordance with the present invention, technique is simple, reaction condition is gentle, easily operation；Required raw material
Be easy to get, cost it is cheap, be adapted to large-scale production.
Obviously, those skilled in the art can carry out the essence of various changes and modification without departing from the present invention to the present invention
God and scope.So, if these modifications and variations of the present invention belong to the scope of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to comprising including these changes and modification.
Claims (8)
1. a kind of preparation method of coronene, it is characterised in that this method includes：
Coupling reaction：Compound shown in the Formula II of compound and 4.2~5.6 equivalents is in catalyst, alkali shown in the Formulas I of 1 equivalent
Under the conditions of existing, coupling reaction is carried out in a solvent, is converted into compound shown in formula III；
Ring closure reaction：Compound shown in formula III carries out ring closure reaction in the presence of Loprazolam or trifluoromethanesulfonic acid, is converted into formula
Coronene shown in IV；
。
2. preparation method according to claim 1, it is characterised in that in the coupling reaction, the catalyst is selected from
Tetra-triphenylphosphine palladium, Pd/C, two (triphenylphosphine) palladium chlorides；The alkali is selected from potassium carbonate, sodium carbonate, sodium hydroxide, three water
Close potassium phosphate, anhydrous phosphoric acid potassium.
3. preparation method according to claim 1, it is characterised in that in the coupling reaction, compound shown in Formula II
Dosage be 4.4~5.0 equivalents.
4. preparation method according to claim 1, it is characterised in that the solvent of the coupling reaction is toluene and ethanol
Mixture, the mixture of toluene and methanol, toluene and the mixture of second alcohol and water, DMF, DMF and water mixture, tetrahydrochysene furan
Mutter, mixture, glycol dimethyl ether, the glycol dinitrate of the mixture of tetrahydrofuran and water, dioxane, dioxane and water
The mixture of ether and water.
5. according to any described preparation method of Claims 1 to 4, it is characterised in that：
In the coupling reaction, reaction temperature is 60~90 DEG C, and the reaction time is 4~10 hours.
6. preparation method according to claim 1, it is characterised in that the Loprazolam or trifluoromethanesulfonic acid are 5~18
Equivalent.
7. preparation method according to claim 6, it is characterised in that the cyclization step is carried out in dichloromethane solvent
Reaction.
8. preparation method according to claim 7, it is characterised in that when the acid is Loprazolam, solvent is dichloromethane
During alkane；Wherein,
The Loprazolam is added dropwise to reaction system at -10~0 DEG C；
After the Loprazolam is added dropwise, reaction system reacts 90min at 20~30 DEG C, obtains coronene shown in formula IV.
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